I was trying to not make the post have a "Mac is better" tone but it was difficult.
Most of the people I've advised learned on Windows 95 or 98. Those were horrible UX days and helped formed a lot of bad habits.
I've never had to switch someone to Windows and I've always wondered what sort of experience it would be. Coming from OS X I think they would have a better understanding of "the basics" but I wonder how this teaching style would apply to someone using Windows for the very first time.
They're getting an OS they don't understand anyway. They're "starting from 0", in a way.
It also helps that OS X doesn't bother you all that much with it unless it's actually important.